Batyl Alcohol → 1-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol

HRID 2629

Reaction equation

HRID 2629 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23].[C:25](Cl)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:18]([O:19][CH2:20][CH:21]([CH2:22][O:23][C:25]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[OH:24])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 3681Batyl AlcoholHCID 6456Trityl chloride2×HCID 8471Triethylamine

Product 1

HCID 128968481-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-olYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

51.69 Grams (150 mmol) of batylalcohol and 62.73 g (225 mmol) freshly recrystallized tritylchloride are dissolved at 35° C. in 350 ml methylene chloride. (Note: It is recommended that the tritylchloride be freshly recrystallized from halpasol, trademark for a petroleum ether fraction, b.p. 100°-120° C.). During 15 minutes, 22.77 g (225 mmol; 31.38 ml) triethylamine is added dropwise to the stirred solution at 30°-35° C. (cooling with a water bath). The reaction is continued for six hours at ambient temperature. (Note: It is recommended that a control TLC be done to make sure that the reaction is complete). The solution is then washed with 300 ml of a NaHCO3 solution (1%), dried over anhydrous sodium sulfate, filtered and evaporated under vacuum. The oily residue (155 g) is dissolved in 660 ml acetonitrile by warming up to 70° C. with stirring. After cooling to room temperature the title product crystallizes (preferentially after adding a few seed crystals). Crystallization is completed by standing overnight at ambient temperature. The crystallizate is filtered off to yield 82.5 g (93.7%) of crude product (m.p. 53°-55° C.) which can be used for the following step without purification. Recrystallization from halpasol (310 ml) yields 71 g (80%) of pure tritylbatylalcohol. B. In a similar way, introduction of the 3-O-trityl function is accomplished for each 1-O-R-glycerol of Example 2-B.

Workup

  1. custombe freshly recrystallized from halpasol, trademark for a petroleum ether fraction, b.p. 100°-120° C.)
  2. temperature(cooling with a water bath)
  3. waitThe reaction is continued for six hours at ambient temperature
  4. washThe solution is then washed with 300 ml of a NaHCO3 solution (1%)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. dissolutionThe oily residue (155 g) is dissolved in 660 ml acetonitrile
  9. temperatureAfter cooling to room temperature the title product
  10. customcrystallizes (preferentially
  11. additionafter adding a few seed crystals)
  12. customCrystallization
  13. waitby standing overnight at ambient temperature
  14. filtrationThe crystallizate is filtered off

Sources & evidence

ORD record
ord-0332df00e2284765af8a85ebe5acb072
Source dataset
uspto-grants-1998_03
Patent number
US05730157

Linked notes

Loading…